%0 Generic
%A Shao, Wenjie
%A L. J. Clive, Derrick
%D 2015
%T A Family of Routes to
Substituted Phenols, Including
Meta-Substituted Phenols
%U https://acs.figshare.com/articles/dataset/A_Family_of_Routes_to_Substituted_Phenols_Including_Meta_Substituted_Phenols/2097346
%R 10.1021/acs.joc.5b02187.s001
%2 https://acs.figshare.com/ndownloader/files/3730588
%K electrophile
%K regiochemically
%K ArSR
%K sequence
%K deprotonated
%K compound
%K meta
%K sulfide
%K substituent
%K substitution patterns
%K variety
%K Substituted Phenols
%K PhMe
%K ArSAr
%K Bromo
%K Grignard reagent
%K latter process
%K PhenolsA
%K benzene derivatives
%K phenolic hydroxyl
%K ArSePh
%K benzenediol
%K selenide
%K phenolic azides
%K ArN
%K anion
%K room temperature
%K DBU
%K substitution pattern
%K aromatization
%X A new family of routes
to substituted phenols has been developed.
2-Bromo-3-methoxycyclohex-2-en-1-ones are readily deprotonated at
C-6, and the resulting anions react smoothly with a variety of electrophiles;
treatment with DBU in PhMe at room temperature then results in efficient
aromatization to benzene derivatives of a regiochemically defined
substitution pattern. This sequence affords phenolic azides (ArN3), sulfides (ArSR, ArSAr′), selenides (ArSePh), alcohols
[ArCH(OH)R], amino derivatives [ArCH(NHSO2Ar′)R),
and 1,2-benzenediols. A complementary set of substitution patterns
is obtained by DIBAL-H reduction or reaction with a Grignard reagent
before aromatization; the latter process gives compounds in which
the newly introduced substituent is meta to the phenolic hydroxyl.
%I ACS Publications